Investing in Artists of a Company
Why Founders are Artists in Their Own Right
It’s a very interesting and complex time in venture. There are undoubtedly still notes of a bear market— net new ARR is down across the board, many companies are avoiding going to market in fear of down rounds, and macro headwinds are being felt in varying degrees. Yet, take a look at the valuations of companies building with the words “generative AI” in their pitch deck, and something will feel eerily similar to the tech bull run in 2020 and 2021.
New technology is always radically additive to the startup ecosystem, but the second-order effects of those new technologies are often hype cycles which make it significantly difficult to separate the signal from the noise; to differentiate between what will endure and what will fall just as fast as it rose to prominence.
One razor which I’ve developed to try to sort the signal from the noise is that of being in search of something that I like to call artists of a company. There is something enlivening about entrepreneurs who are not just building a product or growing a company, but really creating a work of art— something that’s their life’s work, something that emerges from a way of being in and seeing the world, something that is truly beautiful. As someone who primarily looks at software businesses, there is some feeling that seeing beautiful software evokes— a feeling similar to that of seeing a beautiful piece of art, whether it’s a painting, poetry, or work of architecture. It’s a feeling of once you see it, you can’t unsee it; it’s mind-expanding, and it changes your eyes.
Once I internalized how seemingly disparate creations are all under the umbrella of being a beautiful work of art, more connections between great company-builders and other great artists (writers, painters, and musicians for example) began to emerge. This piece is my way of sharing some of the connections I’ve observed so far— let’s dive in.
Creation Begins With Perception
True art emerges not from what one creates, but from what one notices. It’s seeing beauty in the quotidian, extraordinary in the mundane, and noticing the subtle yet important notes which contain a sea of meaning. It’s the perception of the world, what the artist is able to see that nobody else can, that manifests in the work of art that they create.
As Rick Rubin has written:
"Through the ordinary state of being, we're already creators in the most profound way, creating our experience of reality and composing the world we perceive... To live as an artist is a way of being in the world. A way of perceiving. A practice of paying attention. Refining our sensitivity to tune in to the more subtle notes. Looking for what draws us in and what pushes us away. Noticing what feeling tones arise and where they lead."
Every great company starts not with a line of code, but with a deeply authentic insight. A point of view, a perspective, something that the founders notice in the world that strikes a chord of resonance. For Brian Chesky and Joe Gebbia at Airbnb, it was that unoccupied bedrooms in houses and apartments were somewhat like underutilized assets, and that renting them out could foster win-win interactions for all parties involved. For Benoit Dageville and Thierry Cruanes at Snowflake, it was the observation that the integration of storage and compute in database systems led to inefficiencies and unnecessary complexity in the age of big data, and that a new cloud-oriented architecture separating storage and compute could enable enterprises to save both money and time. For Steve Jobs at Apple, it was noticing the magic of the computer— what he called a “bicycle for our minds” — and seeing how the democratization of that technology (from primarily big corporations and research institutions to any household) could result in possibilities that stretched the imagination. In fact, out of all the brilliant entrepreneurs in the last 50 years who’ve built generational businesses, Jobs may have been the most attuned to the entrepreneur as an artist, saying:
“I think great artists and great engineers are similar, in that they both have a desire to express themselves. In fact some of the best people working on the original Mac were poets and musicians on the side. In the seventies computers became a way for people to express their creativity.”
The core insight, what’s noticed and perceived, is the basis layer of all creation; the art is the expression, the manifestation of that. But even to experience a certain revelation or come across a certain insight is not for the faint of the heart; the “aha moment” might be instantaneous but the critical mass of knowledge, context, thought, and experience that enables that one inflection point is enormous. It can’t be reverse engineered nor can it be predicted a priori. The seed of invention gets planted in an artist’s brain in serendipitous moments, but the cultivation of the mental garden to enable that seedling to flourish takes years, and that really is where the art starts.
The Process Is The Reward
There’s a trope in the industry that the best founders are missionaries; they have a deep, insatiable purpose to solve a given problem and bring a new reality into existence, and that’s expressed in the company that they build. Founders of this mission-driven nature prove far more effective than mercenaries, the type of founder who cares more about the material rewards of a successful company (money, status, prestige) than the company’s vision itself.
For true missionaries, the true reward lies not in the output of what is created, but in the journey that it took to get there. There’s a cultivation of a flow state, and the work is autotelic— it’s a means to an end in and of itself. Julian Shapiro articulates this beautifully, saying:
“A craftsperson is someone who makes work the best it can be. Counterintuitively, it’s not output that matters most to the craftsperson. It’s honing a process that generates increasingly good output over time. You cannot be a craftsperson unless the process is the reward.”
Hedonic adaptation has programmed our brain to over-index on the end state, and consequently optimize for reaching certain milestones. The muscle tightens en route to the given milestone, and relaxes upon achievement as the tension of reaching the goal dissipates. For a founder, this milestone could be a number of things— the first round of funding, the first enterprise sale or Fortune 500 customer account, the first instance of reaching $100M in ARR, or even a liquidity event like an acquisition or IPO (which may be the grand goal from day one, for many). It’s commonplace for founders to sprint towards these events, in pursuit of the rewards which they’ll bring, and then gasp for air once they’ve reached the metaphorical finish line. But the best founders know that company building is a marathon, not a sprint. Being purely in search of short-term dopamine hits from micro-achievements with material rewards associated with them won’t sustain for long; the founders who truly endure viscerally know that there is no finish line— to truly actualize a vision and enable it to persist amidst technological and cultural shifts is an endless process. To do this requires a founder to treat their work like a craft, finding fulfillment not only in the milestones or achievements but in late nights, early mornings, and all the brush strokes en route to creating the masterpiece that is their company.
A Founder’s Life’s Work
One belief I have is that the best companies emerge as their founder’s life’s work. The best pieces of art, whether that be a company or a poem, have a certain magnetism to them; an energetic charge composed of the thoughts, insights, feelings, processes, and experiences which compounded over time to enable the art to exist. What reverberates and resonates is not only the artwork itself, but the unseen energetic charge that it carries with it. As Rick Rubin has written:
“Not all projects take time, but they do take a lifetime. In calligraphy, the work is created in one movement of the brush. All the intention is in that single concentrated movement. The line is a reflection of the energy transfer from the artist’s being, including the entire history of their experiences, thoughts, and apprehensions, into the hand. The creative energy exists in the journey to the making, not in the act of constructing.”
The very act of starting a company may be instantaneous, but the cultivation of that mental garden to bring into existence that magnetism takes years. Take the Snowflake founders, for example. Benoit Dageville’s first obsession wasn’t cloud data warehouses, it was a programmable calculator— from when he was a kid growing up in France. This led to an obsession with programming, which led to a Ph.D. in computer science with a thesis focused on running SQL on parallel systems to process massive amounts of data (looks like there’s a vector taking shape?). He then went to Oracle in the 1990s, embracing the challenge of working on some of the biggest problems in data management and data processing. It was there where he met his co-founder, Thierry Cruanes, a fellow Ph.D. who had also grown up in France (but for him, it was the Apple Lisa that captivated him).
A decade later, after steeping themselves in data management at Oracle amidst the big data revolution and shift to the cloud, Benoit and Thierry were dissatisfied. Though they had initially come to the company to work on hard technical problems and create new products, 90% of their time was going towards fixing bugs on existing products. They wanted to capitalize on the shift towards cloud computing and be part of the big data revolution, something which they weren’t in the position to do (at the time, keep in mind this is 2012) at a big monolith.
So, while the possibilities of starting Snowflake may have only emerged when Benoit and Thierry got a call from Doug Mohr at Sutter Hill Ventures (Doug was initially asking about them filling a chief technologist role at a portfolio company, but conversations quickly shifted to Mike Speiser wanting to incubate a database company with them), the energetic charge had been built over a number of years. Their initial obsession with computer science, PhDs in the field, a mindset oriented towards creation and solving hard problems, years at Oracle developing expertise in data management, and finally the dissatisfaction of being at a big company and the visceral desire to be building new products— all of these things collectively added up to create that hidden force that brought a certain magnetism to the work of art Benoit and Thierry would create in Snowflake. Even the insight, around the inefficiencies of integrating storage and compute on-premises, was only enabled by their years at Oracle and seeing customers who struggled with expensive and complex computing and wanted a better, cheaper way to process data. With every passing day at Oracle’s Redwood City campuses, the mental garden was being cultivated more and more. It was only a matter of time before a seedling of an idea emerged.
Mike Spesier (who had been developing an energetic charge of his own, having just incubated Pure Storage at Sutter Hill) could see the artistic element from day one, saying: “A real vision comes from somebody who is an artist. I thought these guys were artists.” The rest is history: Speiser incubated the company and served as the interim CEO, with Benoit and Thierry being co-founders and chief technologists (a clear indicator of being a missionary: they cared less about the prestige associated with being a CEO and more about the mission and bringing this new technology into existence). They built in stealth until October of 2014, when they raised a Series B led by Redpoint and had Bob Muglia, a former Microsoft executive, take over as CEO. The team would continue building both the product and the company, surviving scares from a slew of new competitors in the space (including AWS/Amazon’s introduction of Redshift), en route to a 2020 IPO, raising $3.36 billion in what would be the largest software IPO ever.
The same pattern is true for a number of other iconic companies. Think of Logan Green at Lyft, for example. Though the Lyft that we know today may have come into being as a pivot from their initial idea Zimride, the cultivation of Green’s mental garden began in the 1990s, growing up in Los Angeles and driving his 1989 Volvo 740 amidst the transportation chaos that was LA traffic. In his own words, “There were thousands of people heading in the same direction, one person in each car. I thought, If we can just get two people in the car, you could get half these cars off the road.” This incubated a certain interest in public transportation, which grew when he attended UCSB— upon learning about the East Coast car-sharing club Zipcar, he tried to implement the same thing on his college campus. He had the university purchase a small fleet of Toyota Priuses, and subsequently built a system where students could book cars on a website and unlock the doors of those cars with radio ID cards and access codes.
This experience, combined with experiments with Craigslist's ridesharing channel and becoming the youngest board member of the Santa Barbara Transit Board, collectively compounded the energetic charge and cultivated the mental garden which would be of importance when serendipity soon struck. The serendipitous seedling of the idea emerged while on a trip to Africa with his high school best friend Matt Van Horn; in Zimbabwe, where few people owned a car, Green and Van Horn observed people piling into minivans driven by unlicensed taxi drivers and were in awe of the efficiency. The revelation was that, as Van Horn would say, “it didn’t make sense to drive a car unless every seat was filled and everyone was paying a little bit of gas money.” This serendipitous experience seeded the idea of Zimride, a product harnessing the internet to try to fill every open seat of every car.
Logan Green launched Zimride (and their first app, Carpool) at the perfect time: the new social service Facebook enabled the app to get some traction among college students, and it was a matter of time before Cornell graduate John Zimmer saw the app and was filled with awe and wonder. Zimmer seemed to be the perfect fit as a co-founder for the new startup that was Zimride: having studied hotel administration at Cornell, he knew that the two must-haves for a successful (and profitable) hotel were 1) high occupancy and 2) great hospitality. He saw that the transportation industry, as it was constructed at the time, had neither; this cross-pollination of ideas revealed to him that transportation was ripe for reinvention. He soon got a friend to introduce him to Logan Green, and in 2008, the two made their way to Silicon Valley to raise venture money (Floodgate did the seed round in 2010, Mayfield led the Series A in 2011) and build the carpooling service business. The grand pivot happened in 2012, when they built a mobile version of Zimride and expanded the scope of their product, going from the initial product of daily commutes and long trips to any ride, any time, that goes from one point to another within a big city. Though they initially called this Zimride Instant, the work of art soon took another name: Lyft.
For both Benoit and Thierry at Snowflake and Logan and John at Lyft, the companies that they created had a certain magnetism to it. It was a work of art, their life’s work, which emerged out of how they saw the world and how that perception of reality manifested in the products and companies they built. These are the types of founders who will survive in any market condition; residents, not tourists. Builders who will build regardless of the weather or the climate, because doing so is not just an opportunistic way to take advantage of a certain trend- it’s a calling, their life’s work, what they were put on this planet to do. As we embark on this AI wave and see many intriguing companies be built over the next 5-10 years, the number one thing I’m looking for in teams is a magnetism, an energetic charge, embedded within the true artists of a company. Because a founder truly is an artist, just as much as a painter or a writer is.